Bethenny Frankel’s ex-boyfriend has died, according to TMZ. News just broke that Dennis Shields, one of her most recent love interests, was found dead of a suspected overdose Friday.

TMZ reports that law enforcement got a call around 9 a.m. for an “unresponsive male” at Trump Tower in New York City. They arrived at his apartment to find a lifeless Shields, says the Hollywood Reporter. TMZ says the 51-year-old’s assistant “administered Narcan but was unsuccessful in reviving him.” Narcan is a drug used to treat narcotic overdoses in emergencies and was recently used successfully on Demi Lovato.

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Sources told the New York Post that Shields asked his assistant to administer Narcan, “believing he was overdosing on prescription pills.” Unfortunately, he lost consciousness before the medication kicked in. He was pronounced dead a short time later.

TMZ’s sources say Shields overdosed on the painkiller oxycodone.

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Frankel, a star of The Real Housewives of New York City, had known Shields, the CEO of LawCash, for about 30 years; she once tweeted that she went to high school with his ex-wife. However, the pair started dating only in 2016. Since then, they’ve been on and off. Earlier this year, Frankel opened up to Steve Harvey about their complicated relationship. “I’ve been with someone on and off for years,” she said on Harvey’s show, without identifying Shields by name. “It’s like a partnership where if we’re not being teammates and it’s not working and one man is down, then the other man is down. … We’re trying to really kind of be good partners and be good teammates, and I think relationships, oddly, are — and this sounds cold, but a little bit like business,” she added. “If both people aren’t happy about it but slightly uncomfortable and giving up something or giving in [to] something, it doesn’t work. So both partners have to say, ‘All right, I’m in it for this.'”

Shields made a few appearances on the show but mostly avoided cameras. However, during the crew’s Season 10 trip to Cartagena, Colombia, Frankel called him in a panic because she wanted to go home. The episode aired a few weeks ago.